Drake & Rihanna's Relationship Timeline Shows Just How Much They Keep Everyone Guessing

When Rihanna released her new album ANTI, she included a track with Drake called "Work." Suddenly, it felt like pop culture jumped back a few years and it was 2010 all over again. After all, that was when Drake and RiRi first collaborated on "What's My Name?" In the music video, things got pretty heated in the milk aisle at the grocery store. Then, they made music again in 2012 and created another flirtatious video for Drizzy's song "Take Care." I'm sensing a pattern here: Record a song together, make a video, and restart the cycle of speculation about their love life.

For years, these singers have been the subject of on-again, off-again dating rumors. I can't be the only one wondering, did these two actually ever date? The answer is yes — well, kind of. (More on that later.) Plus, Chris Brown came back into the picture at one point, so things were bound to get messy. Their love triangle definitely reached its breaking point in 2012, but luckily, things are all good now.

May 2009

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The rumors began back in 2009 at Lucky Strikes Lanes & Lounge, a bowling alley in New York City. Page Six reported that Rihanna and Drake were spotted making out. There was whiskey and apple juice involved.

June 2010

I could tell it wasn't love, I just thought you'd f*ck with meWho could've predicted Lucky Strikes would have you stuck with me?What happened between us that night it always seems to trouble meNow all of a sudden these gossip sites wanna cover meAnd you making it seem like it happened that way because of meBut I was curious and I never forget it, baby, what an experienceYou could've been the one, but it wasn't that serious

You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, wow, this feels terrible.

October/November 2010

RihannaVEVO on YouTube

I suppose Drake didn't feel too "terrible," because later that year, the pair released "What's My Name?" together. In the song's video, the two cuddle up and get flirty at the grocery store. They're too distracted to cry over the spilled milk.

November 2015

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Just when you thought the whole story makes sense and wraps up nicely, Rihanna told Vanity Fair in November 2015 that her last "real, official boyfriend" was Brown. In other words, the fling with Drake didn't even count as something substantial in her mind. Poor, Drizzy!

January 2016

RihannaVEVO on YouTube

Despite Ri's comments in Vanity Fair, it wasn't enough to deter the "Started From The Bottom" singer. The two collaborated on "Work" for Rihanna's latest album.

Fans will just have to wait and see what happens next. Maybe the timing will finally be right and Drake will get his "ultimate fantasy" once and for all.